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      Pyrrolizidine Alkaloids: Chemistry, Pharmacology, Toxicology and Food Safety

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          Abstract

          Pyrrolizidine alkaloids (PA) are widely distributed in plants throughout the world, frequently in species relevant for human consumption. Apart from the toxicity that these molecules can cause in humans and livestock, PA are also known for their wide range of pharmacological properties, which can be exploited in drug discovery programs. In this work we review the current body of knowledge regarding the chemistry, toxicology, pharmacology and food safety of PA.

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          Pyrrolizidine alkaloids--genotoxicity, metabolism enzymes, metabolic activation, and mechanisms.

          Peter P. Fu, Qingsu Xia, Ge Lin … (2004)
          Pyrrolizidine alkaloid-containing plants are widely distributed in the world and are probably the most common poisonous plants affecting livestock, wildlife, and humans. Because of their abundance and potent toxicities, the mechanisms by which pyrrolizidine alkaloids induce genotoxicities, particularly carcinogenicity, were extensively studied for several decades but not exclusively elucidated until recently. To date, the pyrrolizidine alkaloid-induced genotoxicities were revealed to be elicited by the hepatic metabolism of these naturally occurring toxins. In this review, we present updated information on the metabolism, metabolizing enzymes, and the mechanisms by which pyrrolizidine alkaloids exert genotoxicity and tumorigenicity.
          Article 0 comments Cited 106 times – based on 0 reviews     Review now
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            Hepatic sinusoidal obstruction syndrome associated with consumption of Gynura segetum.

            Feng Wang, Ge Lin, Yan Zhou … (2011)
            One major cause of hepatic sinusoidal obstruction syndrome (HSOS) is the intake of pyrrolizidine alkaloid (PA)-containing products. Over 8000 PA-induced HSOS cases have been reported worldwide and at least 51 among them were suspected to be attributed to exposure to the Chinese medicine 'Tusanqi'. PA-induced hepatotoxicity involves cytochrome P450-mediated metabolic activation of PAs to electrophilic pyrrolic metabolites which react with macromolecules, such as proteins. However, no studies have found such protein adduction in HSOS patients. We report one HSOS case confirmed by liver biopsy, where the patient claimed taking 'Tusanqi' as self-medication. The herb was analyzed by HPLC-MS, and its induced hepatotoxicity in rats was assessed by monitoring the alteration of serum ALT level and liver morphology. Blood pyrrole-protein adducts were determined by UPLC-MS. The herb the patient consumed was identified as Gynura segetum, an erroneous substitute of non-PA-containing Sedum aizoon, called 'Tusanqi'. Hepatotoxic PAs senecionine and seneciphylline were detected in G. segetum. In the PA-exposed patient, serum pyrrole-protein adducts were detected by a newly developed analytical approach. The animal study showed a good correlation of liver injury with the ingestion of G. segetum. For the first time, serum pyrrole-protein adducts were unequivocally detected in a PA-induced HSOS patient, and such adducts show a potential to be developed as a biomarker for the assessment of PA-induced HSOS. Similar to the well-known case of aristolochic acid-poisoning, the observed HSOS was confirmed to arise from the consumption of PA-containing G. segetum, an erroneous substitute of non-PA-containing S. aizoon. Copyright © 2010 European Association for the Study of the Liver. Published by Elsevier B.V. All rights reserved.
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              Flavonoids as acetylcholinesterase inhibitors: Current therapeutic standing and future prospects

              Marya, Seema Patel, Haroon Khan … (2018)
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                Author and article information

                Journal
                Journal ID (nlm-ta): Int J Mol Sci
                Journal ID (iso-abbrev): Int J Mol Sci
                Journal ID (publisher-id): ijms
                Title: International Journal of Molecular Sciences
                Publisher: MDPI
                ISSN (Electronic): 1422-0067
                Publication date (Electronic): 05 June 2018
                Publication date Collection: June 2018
                Volume: 19
                Issue: 6
                Electronic Location Identifier: 1668
                Affiliations
                REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, nº 228, 4050-313 Porto, Portugal; rutemartinsmoreira@ 123456hotmail.com (R.M.); valentao@ 123456ff.up.pt (P.V.)
                Author notes
                [* ]Correspondence: dpereira@ 123456ff.up.pt (D.M.P.); pandrade@ 123456ff.up.pt (P.B.A.); Tel.: +351-220-428-655 (D.M.P.); +351-220-428-654 (P.B.A.)
                Author information
                https://orcid.org/0000-0003-0384-7592
                https://orcid.org/0000-0002-0740-4396
                https://orcid.org/0000-0002-9764-3920
                Article
                Publisher ID: ijms-19-01668
                DOI: 10.3390/ijms19061668
                PMC ID: 6032134
                PubMed ID: 29874826
                SO-VID: 021b7228-0a13-4ee9-a829-9f28b22289c5
                Copyright © © 2018 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 19 April 2018
                Date accepted : 23 May 2018
                Categories
                Subject: Review

                ScienceOpen disciplines: Molecular biology
                Keywords: pyrrolizidine alkaloids,chemistry,toxicity,pharmacological properties,food safety
                Data availability:
                ScienceOpen disciplines: Molecular biology
                Keywords: pyrrolizidine alkaloids, chemistry, toxicity, pharmacological properties, food safety

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